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Catalytic asymmetric synthesis using chirality‑switchable helical polymer as a chiral ligand

✍ Scribed by Suginome, Michinori (author);Yamamoto, Takeshi (author);Nagata, Yuuya (author);Yamada, Tetsuya (author);Akai, Yuto (author)

Book ID
115474802
Publisher
International Union of Pure and Applied Chemistry
Year
2012
Tongue
English
Weight
613 KB
Volume
84
Category
Article
ISSN
0033-4545

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✦ Synopsis

Single-handed PQXphos, i.e., helical poly(quinoxaline-2,3-diyl)s bearing diarylphosphino pendant groups, served as remarkable chiral ligands in palladium-catalyzed asymmetric hydrosilylation of styrenes and asymmetric biaryl synthesis by Suzuki–Miyaura coupling, affording up to 98 % enantiomeric excess (e.e.) in both reactions. A palladium complex of high-molecular-weight variant (1000mer) of PQXphos could be reused eight times by virtue of the formation of an insoluble polymer complex. PQXphos underwent solvent-dependent inversion of the helical sense, enabling production of either of two enantiomeric products using a single PQXphos.

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Catalytic asymmetric synthesis of second
Catalytic asymmetric synthesis of secondary alcohols using chiral cis-1-amino-2-hydroxy-1,2,3,4-tetrahydronaphthalene as chiral ligand
✍ Cristina M Bellucci; Antonio Bergamini; Pier Giorgio Cozzi; Angelo Papa; Emilio 📂 Article 📅 1997 🏛 Elsevier Science 🌐 English ⚖ 529 KB

The synthesis and resolution of cis-1-amino-2-hydroxy-1,2,3,4tetrahydronaphthalene 5 by a simple and straightforward methodology has been achieved. The homochiral aminoalcohol has been used in the catalytic reduction of ketones by means of BH 3 .SMe2 affording secondary alcohols in high enantiomeric